Boc-Gly-SCH2CH2COOH | 133367-03-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Boc-Gly-SCH2CH2COOH
• 英文别名: 3-[2-[(2-Methylpropan-2-yl)oxycarbonylamino]acetyl]sulfanylpropanoic acid
• CAS: 133367-03-0
• 化学式: C₁₀H₁₇NO₅S
• 分子量: 263.315
• InChiKey: MZRRNGYKZBEYEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  118
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Boc-Gly-SCH2CH2COOH 在 三氟乙酸 作用下， 以 水 、 乙腈 为溶剂， 生成 Trp-Lys-His-Pro-Gly-SCH2CH2CONH2
  参考文献：
  名称：

  Development of a Linker with an Enhanced Stability for the Preparation of Peptide Thioesters and Its Application to the Synthesis of a Stable-Isotope-Labelled HU-Type DNA-Binding Protein

  摘要：

  已开发一种含有S-烷基硫酯基团的连接剂，该连接剂在树脂上的稳定性增强。该连接剂含有S-烷基硫酯及间隔基团 –CO–SC(CH3)2CH2CO–Nle–，在肽链延长周期中表现出稳定性。该硫酯在HF处理条件下稳定，并在N-羟基琥珀酰亚胺（HONSu）存在下被银离子迅速激活以形成肽键。利用该连接剂，制备了覆盖细菌杆菌（Bacillus stearothermophilus）HU型DNA结合蛋白（HBs）的肽段，并对其进行了特定标记，标记元素包括2H、13C和15N。利用这些肽段合成了多标记的HBs。通过核磁共振（NMR）光谱检测到了HBs中2H、13C和15N的明显信号。

  DOI：

  10.1246/bcsj.66.2700
• 作为产物：
  描述：

  Boc-甘氨酸-4-硝基苯酯 、 3-巯基丙酸 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 以91.6%的产率得到Boc-Gly-SCH2CH2COOH
  参考文献：
  名称：

  Polypeptide Synthesis Using theS-Alkyl Thioester of a Partially Protected Peptide Segment. Synthesis of the DNA-Binding Domain ofc-Myb Protein (142–193)–NH₂

  摘要：

  已经开发出一种使用部分受保护的肽片段的S-烷基硫酯合成多肽的方法。通过这种方法合成了 c-Myb 蛋白 (142-193) 的 DNA 结合域，以评估其有用性。部分受保护的肽片段 Boc–[Lys(Boc)143,144,160]–c-Myb 蛋白(142–163)–SCH2CH2CONH2 和 [Lys(Boc)171,182,192]–c-Myb 蛋白(164–193)–NH2 高度受保护。从通过固相方法获得的肽中纯化。在银离子和对硝基苯酚存在下，肽链段羧基部分的硫酯转化为相应的对硝基​​苯酯，然后两个链段缩合。偶联反应几乎完全进行，在去除 Boc 基团后产生高度纯化的产物。

  DOI：

  10.1246/bcsj.64.111

文献信息

• Application of a novel thioesterification reaction to the synthesis of chemokine CCL27 by the modified thioester method
  作者：Hironobu Hojo、Yuichi Murasawa、Hidekazu Katayama、Tsuyoshi Ohira、Yuko Nakahara、Yoshiaki Nakahara

  DOI：10.1039/b800884a

  日期：——

  Aryl thioesters of peptide segments were prepared by the conventional 9-fluorenylmethoxycarbonyl (Fmoc) strategy using a novel N-alkyl cysteine (NAC)-assisted thioesterification reaction. The peptide carrying NAC at its C-terminus was prepared by the Fmoc strategy and converted to the aryl thioester by 4-mercaptophenylacetic acid (MPAA) treatment without significant side reactions. The peptide thioester was used for the efficient preparation of 95-amino acid (AA) chemokine CCL27 by an Ag+-free thioester method.

  通过改进的N-烷基半胱氨酸(NAC)辅助硫酯化反应，采用传统的9-芴甲氧羰基(Fmoc)策略制备了肽段的芳基硫酯。含有C端NAC的肽段通过Fmoc策略制备，并通过4-巯基苯乙酸(MPAA)处理转化为芳基硫酯，过程中未发生显著的副反应。这种肽硫酯被用于高效制备95个氨基酸的趋化因子CCL27，采用无Ag+的硫酯方法。
• Synthesis of Peptide Thioacids at Neutral pH Using Bis(2-sulfanylethyl)amido Peptide Precursors
  作者：Silvain L. Pira、Emmanuelle Boll、Oleg Melnyk

  DOI：10.1021/ol402601j

  日期：2013.10.18

  Reaction of bis(2-sulfanylethyl)amido (SEA) peptides with trilsopropylsilylthiol in water at neutral pH yields peptide thiocarboxylates. An alkylthioester derived from beta-alanine was used to trap the released bis(2-sulfanylethyl)amine and displace the equilibrium toward the peptide thiocarboxylate.
• Development of a Linker with an Enhanced Stability for the Preparation of Peptide Thioesters and Its Application to the Synthesis of a Stable-Isotope-Labelled HU-Type DNA-Binding Protein
  作者：Hironobu Hojo、Yeondae Kwon、Yoshimitsu Kakuta、Sakae Tsuda、Isao Tanaka、Kunio Hikichi、Saburo Aimoto

  DOI：10.1246/bcsj.66.2700

  日期：1993.9

  An S-alkyl-thioester-moiety-containing linker with an enhanced stability on a resin has been developed. A linker containing S-alkyl thioester with a spacer group, –CO–SC(CH3)2CH2CO–Nle–, was stable during the peptide chain elongation cycle. This thioester was stable under HF treatment conditions, and was rapidly activated by silver ions in the presence of N-hydroxysuccinimde (HONSu) to form a peptide bond. Using this linker, peptide segments covering the HU-type DNA-binding protein of Bacillus stearothermophilus (HBs), which was site-specifically labelled with 2H, 13C, and 15N, were prepared. Using these peptide segments, multi-labelled HBs was synthesized. Distinct signals of 2H, 13C, and 15N in HBs were detected by NMR spectrometry.

  已开发一种含有S-烷基硫酯基团的连接剂，该连接剂在树脂上的稳定性增强。该连接剂含有S-烷基硫酯及间隔基团 –CO–SC(CH3)2CH2CO–Nle–，在肽链延长周期中表现出稳定性。该硫酯在HF处理条件下稳定，并在N-羟基琥珀酰亚胺（HONSu）存在下被银离子迅速激活以形成肽键。利用该连接剂，制备了覆盖细菌杆菌（Bacillus stearothermophilus）HU型DNA结合蛋白（HBs）的肽段，并对其进行了特定标记，标记元素包括2H、13C和15N。利用这些肽段合成了多标记的HBs。通过核磁共振（NMR）光谱检测到了HBs中2H、13C和15N的明显信号。
• Polypeptide Synthesis Using the<i>S</i>-Alkyl Thioester of a Partially Protected Peptide Segment. Synthesis of the DNA-Binding Domain of<i>c</i>-Myb Protein (142–193)–NH₂
  作者：Hironobu Hojo、Saburo Aimoto

  DOI：10.1246/bcsj.64.111

  日期：1991.1

  A method for polypeptide synthesis using S-alkyl thioester of a partially protected peptide segment has been developed. The DNA-binding domain of c-Myb protein (142–193) was synthesized by this method to estimate its usefulness. The partially protected peptide segments, Boc–[Lys(Boc)143,144,160]–c-Myb protein(142–163)–SCH2CH2CONH2 and [Lys(Boc)171,182,192]–c-Myb protein(164–193)–NH2, were highly purified from peptides obtained by a solid-phase method. The thioester in the carboxyl component of the peptide segment was converted to the corresponding p-nitrophenyl ester in the presence of silver ions and p-nitrophenol and then the two segments were condensed. The coupling reaction proceeded almost completely yielding a highly-purified product after removal of Boc groups.

  已经开发出一种使用部分受保护的肽片段的S-烷基硫酯合成多肽的方法。通过这种方法合成了 c-Myb 蛋白 (142-193) 的 DNA 结合域，以评估其有用性。部分受保护的肽片段 Boc–[Lys(Boc)143,144,160]–c-Myb 蛋白(142–163)–SCH2CH2CONH2 和 [Lys(Boc)171,182,192]–c-Myb 蛋白(164–193)–NH2 高度受保护。从通过固相方法获得的肽中纯化。在银离子和对硝基苯酚存在下，肽链段羧基部分的硫酯转化为相应的对硝基​​苯酯，然后两个链段缩合。偶联反应几乎完全进行，在去除 Boc 基团后产生高度纯化的产物。